Sodium Iodide → HCID 57642375, compound

HRID 2112495Notes

Reaction equation

HRID 2112495 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[C:23]([C:24]#[N:25])=[CH:22][C:8]2[C:9]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[Cl:21])=[N:10][CH2:11][C:12](=[O:14])[NH:13][C:7]=2[CH:6]=1.[CH3:26][O:27][CH2:28][CH2:29][N:30](C)[CH2:31]CO.[I-].[Na+]>O1CCCC1>[Cl:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:9]1[C:8]2[CH:22]=[C:23]([C:24]#[N:25])[C:5]([O:4][CH2:3][CH2:2][N:30]([CH2:29][CH2:28][O:27][CH3:26])[CH3:31])=[CH:6][C:7]=2[NH:13][C:12](=[O:14])[CH2:11][N:10]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 22030569HCID 22030569, compoundHCID 57642376HCID 57642376, compound

Product 1

HCID 57642375HCID 57642375, compoundYield 17.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
83 °C

Procedure

A mixture of 1.2 g (0.0032 mole) of 8-(2-chloroethoxy)-5-(2-chlorophenyl)-7-cyano-1,3-dihydro-2H-1,4-benzodiazepin-2-one (Iss, prepared in Example 35), 2.85 g (0.032 mole) of 2-((2-methoxyethyl)methylamino) ethanol, 20 mL of tetrahydrofuran and 4.8 g (0.032 mole) of sodium iodide was heated in an oil bath at 83° C. under an argon atmosphere for 20 hours. The mixture was cooled and then partitioned between ethyl acetate and 0.6 M sodium bicarbonate solution. The ethyl acetate layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was chromatographed on silica gel, eluting with acetonitrile-methanol (80:20) to give 0.233 g of 5-(2-chlorophenyl)-7-cyano-1,3-dihydro-8-(2-((2-methoxyethyl)methylamino)-ethoxy)-2H-1,4-benzodiazepin-2-one (Iv).

Workup

  1. temperatureThe mixture was cooled
  2. custompartitioned between ethyl acetate and 0.6 M sodium bicarbonate solution
  3. washThe ethyl acetate layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was chromatographed on silica gel
  8. washeluting with acetonitrile-methanol (80:20)

Sources & evidence

ORD record
ord-58268a87acac42dfa916205c7f51f1d6
Source dataset
uspto-grants-2009_04
Patent number
US07524840B2

Reaction notes

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